HETEROGENEOUS COPPER-CATALYZED SYNTHESIS OF S-ARYLATED 2-AMINOTHIOPHENOLS VIA RING OPENING OF BENZOTHIAZOLES AND C-S COUPLING USING ARYL HALIDES

被引:0
作者
Ichikawa, Tomohiro [1 ]
Matsuo, Tomohiro [1 ]
Tachikawa, Takumu [1 ]
Sawama, Yoshinari [1 ]
Monguchi, Yasunari [2 ]
Sajiki, Hironao [1 ]
机构
[1] Gifu Pharmaceut Univ, Lab Organ Chem, 1-25-4 Daigaku Nishi, Gifu 5011196, Japan
[2] Daiichi Univ Pharm, Lab Organ Chem, Minami Ku, 22-1 Tamagawa Cho, Fukuoka, Fukuoka 8158511, Japan
关键词
CHEMOSELECTIVE HYDROGENATION; PALLADIUM CATALYST; UNSATURATED BONDS; SILK-FIBROIN; SULFUR; IODIDES;
D O I
10.3987/COM-18-S(T)55
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Chelate resins, which are polystyrene-divinylbenezene-based polymers bearing iminodiacetic acids or polyamines as ligands, supported copper catalysts (Cu/CR11 or Cu/CR20) in effectively catalyzing the ring cleaving S-arylation of benzothiazole with aryl iodides or aryl bromides in the presence of lithium tert-butoxide in aqueous 2-propanol.
引用
收藏
页码:793 / 805
页数:13
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共 43 条
  • [1] Characterization of synthetic adsorbents with fine particle sizes for preparative-scale chromatographic separation
    Adachi, T
    Ando, S
    Watanabe, J
    [J]. JOURNAL OF CHROMATOGRAPHY A, 2002, 944 (1-2) : 41 - 59
  • [2] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions
    Beletskaya, Irina P.
    Ananikov, Valentine P.
    [J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1596 - 1636
  • [3] Sulfur and Its Role In Modern Materials Science
    Boyd, Darryl A.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (50) : 15486 - 15502
  • [4] Organocatalytic Carbon-Sulfur Bond-Forming Reactions
    Chauhan, Pankaj
    Mahajan, Suruchi
    Enders, Dieter
    [J]. CHEMICAL REVIEWS, 2014, 114 (18) : 8807 - 8864
  • [5] Heterogeneous Catalysts for the One-Pot Synthesis of Chemicals and Fine Chemicals
    Climent, Maria J.
    Corma, Avelino
    Iborra, Sara
    [J]. CHEMICAL REVIEWS, 2011, 111 (02) : 1072 - 1133
  • [6] Transition Metal Catalyzed Synthesis of Aryl Sulfides
    Eichman, Chad C.
    Stambuli, James P.
    [J]. MOLECULES, 2011, 16 (01): : 590 - 608
  • [7] Sulfur Containing Scaffolds in Drugs: Synthesis and Application in Medicinal Chemistry
    Feng, Minghao
    Tang, Bingqing
    Liang, Steven H.
    Jiang, Xuefeng
    [J]. CURRENT TOPICS IN MEDICINAL CHEMISTRY, 2016, 16 (11) : 1200 - 1216
  • [8] Unexpectedly ligand-free copper-catalyzed C-S cross-coupling of benzothiazole with aryl iodides in aqueous solution
    Feng, Yi-Si
    Qi, Hong-Xia
    Wang, Wei-Cheng
    Liang, Yu-Feng
    Xu, Hua-Jian
    [J]. TETRAHEDRON LETTERS, 2012, 53 (23) : 2914 - 2917
  • [9] Iodine-Mediated Difunctionalization of Imidazopyridines with Sodium Sulfinates: Synthesis of Sulfones and Sulfides
    Guo, Yu-Jing
    Lu, Shuai
    Tian, Lu-Lu
    Huang, En-Ling
    Hao, Xin-Qi
    Zhu, Xinju
    Shao, Tian
    Song, Mao-Ping
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (01) : 338 - 349
  • [10] Evolution of a Fourth Generation Catalyst for the Amination and Thioetherification of Aryl Halides
    Hartwig, John F.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2008, 41 (11) : 1534 - 1544